Senior Director, Billings and Collections
Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.
Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.
The Director of Billing and Collections will be responsible for building and leading the company's billing and collections function as we scale our Workers' Compensation and Commercial Auto Insurance business. This leader will be responsible for ensuring accurate, timely, and compliant premium invoicing and collections while reducing outstanding receivables and improving cash flow.
The ideal candidate will have deep experience in P&C insurance billing, regulatory compliance, and collections strategies. This person will drive automation, improve efficiency, and implement best practices to scale our billing operations in a high-growth environment.
How Youll Do It
Billing & Collections Strategy & Execution:
Own the end-to-end premium billing process, ensuring timely and accurate invoicing for Workers Compensation and Commercial Auto insurance policies.
Develop and optimize collections strategies to reduce DSO (Days Sales Outstanding) and minimize bad debt exposure.
Oversee audit premium adjustments, cancellations, and policyholder refunds, ensuring compliance with state and regulatory requirements.
Collaborate with underwriting, policy administration, and claims teams to align billing with policy lifecycle changes.
Process Optimization & Technology:
Automate billing & collections workflows to increase efficiency and reduce errors.
Implement and optimize billing and payment platforms (e.g., Zuora, Guidewire, Duck Creek, One Inc, Stripe, or similar).
Introduce AI-driven collections strategies (e.g., predictive scoring for delinquent accounts).
Enhance customer payment experience, including self-service options and flexible payment plans.
Regulatory Compliance & Risk Management:
Ensure compliance with state regulations governing premium billing and collections in Workers Comp & Commercial Auto.
Lead audits, reporting, and reconciliation efforts to maintain compliance with NAIC, state insurance departments, and GAAP accounting standards.
Develop and enforce collections policies, including handling of delinquent accounts and coordination with legal teams on recoveries.
Team Leadership & Cross-Functional Collaboration:
Build and lead a high-performing billing and collections team.
Work closely with sales and customer service teams to improve payment adherence while maintaining strong client relationships.
Partner with finance and treasury teams to ensure accurate cash flow forecasting, financial statement reporting, subledger support and reconciliation.
The Right Stuff
Bachelors degree in finance, accounting, or business required.
Minimum of 12 years of experience in premium billing, collections, or revenue cycle management in P&C insurance, preferably focused on Workers Compensation and Commercial Auto.
Minimum of 10 years of leadership/management experience.
Expertise in billing automation, ERP systems, and collections platforms (Guidewire, Duck Creek, One Inc, Netsuite, Workday, etc.).
Deep knowledge of regulatory compliance (state-by-state billing laws, premium audits, cancellation & reinstatement policies).
Data-driven approach, with experience using SQL, Tableau, or Excel to analyze billing trends and optimize collections.
Excellent stakeholder management skills, with the ability to collaborate across Finance, Operations, Underwriting, and IT.
Strong attention to detail.
Excellent analytical, problem-solving, and organizational skills.
Strong communication and interpersonal skills.
Base Compensation Range
$200,000$250,000 USD
Compensation & Benefits
Competitive cash compensation
A piece of the pie (in the form of equity)
Comprehensive health plans
Generous PTO
Future focused 401k match
Generous parental and caregiver leave
Our core values are more than just a poster on the wall; theyre tangibly reflected in our work
Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When weve identified a talented individual who wed like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidates knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges.
Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.
Location Information
Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver office and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet.
Additional Information
Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.
Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.
Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy.
Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.
Pie Insurance Announces $315 Million Series D Round of Funding
Built In honors Pie in its 2024 Best Places to Work Awards
Pie Insurance Named a Leading Place to Work in Colorado
#LI-REMOTE
#BI-REMOTE
Apply Now
Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.
The Director of Billing and Collections will be responsible for building and leading the company's billing and collections function as we scale our Workers' Compensation and Commercial Auto Insurance business. This leader will be responsible for ensuring accurate, timely, and compliant premium invoicing and collections while reducing outstanding receivables and improving cash flow.
The ideal candidate will have deep experience in P&C insurance billing, regulatory compliance, and collections strategies. This person will drive automation, improve efficiency, and implement best practices to scale our billing operations in a high-growth environment.
How Youll Do It
Billing & Collections Strategy & Execution:
Own the end-to-end premium billing process, ensuring timely and accurate invoicing for Workers Compensation and Commercial Auto insurance policies.
Develop and optimize collections strategies to reduce DSO (Days Sales Outstanding) and minimize bad debt exposure.
Oversee audit premium adjustments, cancellations, and policyholder refunds, ensuring compliance with state and regulatory requirements.
Collaborate with underwriting, policy administration, and claims teams to align billing with policy lifecycle changes.
Process Optimization & Technology:
Automate billing & collections workflows to increase efficiency and reduce errors.
Implement and optimize billing and payment platforms (e.g., Zuora, Guidewire, Duck Creek, One Inc, Stripe, or similar).
Introduce AI-driven collections strategies (e.g., predictive scoring for delinquent accounts).
Enhance customer payment experience, including self-service options and flexible payment plans.
Regulatory Compliance & Risk Management:
Ensure compliance with state regulations governing premium billing and collections in Workers Comp & Commercial Auto.
Lead audits, reporting, and reconciliation efforts to maintain compliance with NAIC, state insurance departments, and GAAP accounting standards.
Develop and enforce collections policies, including handling of delinquent accounts and coordination with legal teams on recoveries.
Team Leadership & Cross-Functional Collaboration:
Build and lead a high-performing billing and collections team.
Work closely with sales and customer service teams to improve payment adherence while maintaining strong client relationships.
Partner with finance and treasury teams to ensure accurate cash flow forecasting, financial statement reporting, subledger support and reconciliation.
The Right Stuff
Bachelors degree in finance, accounting, or business required.
Minimum of 12 years of experience in premium billing, collections, or revenue cycle management in P&C insurance, preferably focused on Workers Compensation and Commercial Auto.
Minimum of 10 years of leadership/management experience.
Expertise in billing automation, ERP systems, and collections platforms (Guidewire, Duck Creek, One Inc, Netsuite, Workday, etc.).
Deep knowledge of regulatory compliance (state-by-state billing laws, premium audits, cancellation & reinstatement policies).
Data-driven approach, with experience using SQL, Tableau, or Excel to analyze billing trends and optimize collections.
Excellent stakeholder management skills, with the ability to collaborate across Finance, Operations, Underwriting, and IT.
Strong attention to detail.
Excellent analytical, problem-solving, and organizational skills.
Strong communication and interpersonal skills.
Base Compensation Range
$200,000$250,000 USD
Compensation & Benefits
Competitive cash compensation
A piece of the pie (in the form of equity)
Comprehensive health plans
Generous PTO
Future focused 401k match
Generous parental and caregiver leave
Our core values are more than just a poster on the wall; theyre tangibly reflected in our work
Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When weve identified a talented individual who wed like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidates knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges.
Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.
Location Information
Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver office and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet.
Additional Information
Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.
Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.
Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy.
Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.
Pie Insurance Announces $315 Million Series D Round of Funding
Built In honors Pie in its 2024 Best Places to Work Awards
Pie Insurance Named a Leading Place to Work in Colorado
#LI-REMOTE
#BI-REMOTE
Apply Now